Processes for preparing N,N-dihydrocarbylhydroxylamines are known from the prior art.
N,N-dihydrocarbylhydroxylamines are typically prepared by oxidation of the nitrogen atom of the corresponding amines. A disadvantage of the process mentioned is the use of the expensive N,N-dialkylamines as starting compounds.
U.S. Pat. No. 4,876,300 discloses the use of long-chain N,N-dialkylhydroxylamines as stabilizers for polyolefin compositions during their preparation. It is also disclosed that the long-chain N,N-dialkylhydroxylamines used can be prepared by various methods, for example:                oxidation of the corresponding secondary amines by means of aqueous hydrogen peroxide solution in order to obtain the corresponding N,N-dialkyl-hydroxylamines directly,        addition of the corresponding secondary amine onto α,β-unsaturated compounds, for example alkyl acrylates, to obtain the corresponding Michael addition product which is converted in a further process step by means of aqueous hydrogen peroxide solution into the corresponding tertiary amine oxide, and subsequent elimination of the α,β-unsaturated compound to give the N,N-dialkylhydroxylamine,        metathesis reaction between an alkyl halide and a hydroxylamine in the presence of an alkaline compound such as sodium amide, or reaction of an amine with a peroxy compound such as benzoyl peroxide, followed by hydrolysis of the compound formed as an intermediate to give the corresponding hydroxylamine.        
EP 0 495 756 A1 discloses a process for preparing N,N-dihydrocarbylhydroxylamines (RCH2)2NOH from aldehydes and hydroxylamine hydrochloride under hydrogenation conditions in a single-stage process. For this purpose, two equivalents of aldehyde are reacted with hydroxylamine hydrochloride in the presence of hydrogen and a suitable noble metal catalyst to give the corresponding N,N-dihydrocarbylhydroxylamines.